There are a number of questions that plague any operator of a complex data pipeline. How do I quickly recover from failures in my pipeline? How do I know that the data I generate is accurate? How do I minimize the risk associated with updating my pipeline? Designing your data pipeline with resiliency and observability in mind will help to answer these questions. In this talk, I will present several strategies that my team has adopted for reducing operational complexity, risk associated with updates, and concerns about accuracy of data pipelines.